Water → HCID 18667959, compound

HRID 1419763Notes

Reaction equation

HRID 1419763 reaction equation
[H-].[Na+].[N:3]1[O:7][N:6]=[C:5]2[C:8]([OH:12])=[CH:9][CH:10]=[CH:11][C:4]=12.[CH2:13]([CH:15]1[O:17][CH2:16]1)Br.O>CN(C)C=O>[N:3]1[O:7][N:6]=[C:5]2[C:8]([O:12][CH2:13][CH:15]3[O:17][CH2:16]3)=[CH:9][CH:10]=[CH:11][C:4]=12

Participants

6

Reactant 4

HCID 962WaterHCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 135542663HCID 135542663, compound

Product 1

HCID 18667959HCID 18667959, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Sodium hydride (620 mg; 60% oil dispersion) was added in portions to benzofurazan-4-ol (1.74 g) in dimethyl formamide (30ml). The mixture was heated at 50° C. for 30 min. Epibromohydrin (1.6 ml) was added and the mixture was heated at 60° C. for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with water, dried over Na2SO4, and evaporated. The residue was chromatographed on silica gel (50% ethyl acetate/hexane) to give 1-(4-benzofurazanyloxy)-2,3-epoxypropane (1.6 g), mp 75° C.

Workup

  1. temperaturethe mixture was heated at 60° C. for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-19655f9d33b1423fb88b5efcce4921b4
Source dataset
uspto-grants-1999_03
Patent number
US05889007

Reaction notes

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